Why Win The Question Exists

I didn't wake up one day and decide to be an ambitious asshole. I got promoted into it.

The proof came in Chicago. I'd been sent to Y&R Chicago to lead new business, win Miller Brewing, and turn the office around. VP title. Big office. Bigger expense account. I was 30-something and I thought I'd arrived.

In my first six months in the Loop, I was never invited out for team drinks. Not once. And we weren't winning pitches either. I told myself the team was slow to get on board. Inside, the soundtrack was more insecure: I have to prove they made the right call. I have to win.

Then it blew up. I was waiting on the president's assistant to set up a prospect meeting. In my mind, this was obviously the most important item on her list. When it hadn't happened on my timeline, I lost it. I snapped at her in front of other people, as if her job existed mainly to clear my path.

The next day, my president, Kary McIlwain, called me into her office. She didn't yell. She didn't give me a long speech. She just said, very calmly, that I was acting like an asshole and that after yelling at her assistant, nobody wanted to help me.

It landed like a punch. Not because she was cruel. Because she was right.

Here's the thing: I grew up in Midland, a small town where your reputation was built person by person. Around our dinner table, being curious was normal and being heard was expected. I was the kid who asked questions because I actually wanted to know.

That kid went away to college and got rewarded for being smart, fast, and competitive.

Then he went to work in advertising and got rewarded harder. Somewhere in the accumulation of promotions and titles, the small-town instinct to be curious and useful got replaced by a louder need: to win.

When you get addicted to being the person with the answer, every conversation becomes a performance. I wasn't listening to understand. I was listening to reload.

I knew what the problem looked like. I didn't yet know what the fix looked like.

But I had Luke.

Luke Sklar was the best client whisperer I ever saw in action. He co-founded Sklar Wilton, a strategic consulting firm that did serious work for serious brands. While other consultants clicked through slides, Luke stood at the whiteboard, marker in hand, and drew the problem: the client's words, their assumptions, the tensions underneath. Then he'd pause and say, "Let me see if I've got this right," and sketch a cleaner version.

Clients physically leaned in when they talked with Luke. They could see their own thinking getting clearer. Most of the time, Luke wasn't giving them an answer. He was helping them see what they already knew, by asking better questions and listening like the answer was the most important thing in the room.

Years later I realized Kary had done exactly the same thing in that Chicago office. She didn't walk in to win an argument. She came to win a question: what does Scott actually need to hear right now to stop getting in his own way?

That's the whole insight, and it took me longer to learn than I'd like to admit: it's not about you.

Trust runs on simple math. Your credibility, your reliability, and how well you actually know your client, all divided by how much the conversation is about you. David Maister, Charles Green, and Robert Galford captured this in the Trust Equation: credibility, reliability, and intimacy, divided by self-orientation. Everything you bring to the room gets divided by how often you make it about you. Shrink the about you denominator and trust climbs.

Or the way I'd say it to my younger self: Stop trying to win the answer. Start winning the question.

I've spent the last 20 years practicing this and teaching it inside Brainrider, the client-services business I co-founded and still run. Not from a stage looking back at a career. From the room, with clients, every week, getting it wrong less often than I used to.

That practice turned into two things. A book, From Asshole to Ally, coming this fall. And Win The Question, trust training for firms that want their smart people to become their trusted people. The format is simple: real client situations, worked live, with me playing the self-oriented version and the trusted version so your team can see the difference.

This is for ambitious professionals at law, accounting, consulting, advisory, and agency firms, and for the leaders trying to develop them. Ambition isn't the problem. Ambition is the fuel. Most smart professionals just point it at looking smart, when the bigger wins come from being trusted.

Same energy. Better math.

If you lead a team of smart people who haven't become trusted people yet, start with the Trust Quiz.